Sodium Hydroxide → (4-(4-Methoxyphenyl)oxan-4-yl)methanamine

HRID 272806Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([CH2:21][NH2:22])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 7.5 °C

Procedure

To a stirred suspension of LiAlH4 (79 g, 2.08 mol, 5 eq) in THF (900 ml) at 0 to 5° C. under an atmosphere of nitrogen was added 4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonitrile (90 g, 0.414 mol) in THF (900 ml) over a 25 minutes maintaining the temperature at 5 to 10° C. The reaction mixture was allowed to warm to ambient temperature and stirred until complete. Sodium hydroxide (2N, 850 ml) was added dropwise, the resulting solids filtered and washed with THF (2×800 ml), the organics concentrated in vacuo at 40° C. The residue was dissolved in EtOAc (300 ml) and dried over MgSO4, filtered and concentrated in vacuo at 40° C. to provide {[4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-yl]methyl}amine as a light yellow oil (92 g, quantitative).

Workup

temperatureto warm to ambient temperature
filtrationthe resulting solids filtered
washwashed with THF (2×800 ml)
concentrationthe organics concentrated in vacuo at 40° C
dissolutionThe residue was dissolved in EtOAc (300 ml)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo at 40° C.

Sources & evidence

ORD record: ord-2f54fc2fc45d430e85012bf053b4ff9d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456164B2

Reaction notes

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